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7-Hydroxy-4-(2-methyl-allyl)-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester → 7-Hydroxy-4-isobutyl-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

HRID 642339
ノート
印刷プレビュー

反応式

HRID 642339 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([CH2:12][C:13]([CH3:15])=[CH2:14])[C:9]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:18][C:8]=2[C:7]=1[OH:25])=[O:5])[CH3:2]>C(OCC)(=O)C.C(O)C.C(O)=O.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]2[N:16]=[C:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[S:18][C:8]=2[C:7]=1[OH:25])=[O:5])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 1

HCID 684283547-Hydroxy-4-(2-methyl-allyl)-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

生成物 1

HCID 684281637-Hydroxy-4-isobutyl-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester収率 27.3%

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 284Formic Acid溶媒HCID 702Ethanol溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

A mixture of 7-hydroxy-4-(2-methyl-allyl)-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (128 mg, 0.36 mmole) and 10% Pd/C (100 mg) in ethyl acetate (12 ml), ethanol (3 ml) and formic acid (15 μl) was hydrogenated at 20 psi for a week before it was filtered, concentrated and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The sodium bicarbonate layer was washed with dichloromethane. The organic layer was combined and washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a white solid (35 mg). MS: (+) m/z 356.96 (M+1).

後処理

  1. waitwas hydrogenated at 20 psi for a week before it
  2. filtrationwas filtered
  3. concentrationconcentrated
  4. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  5. washThe sodium bicarbonate layer was washed with dichloromethane
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

出典と根拠

ORDレコード
ord-60a124e66db54f73bda029e8512c57f8
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07696223B2

反応ノート

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